222739-25-5

Basic information

• Product Name: 6-oxo-N-<carbonyl>-L-norleucine phenylmethyl ester
• Synonyms: 6-oxo-N-<carbonyl>-L-norleucine phenylmethyl ester
• CAS NO: 222739-25-5
• Molecular Weight: 385.417
• Mol File: 222739-25-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-oxo-N-<carbonyl>-L-norleucine phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-oxo-N-<carbonyl>-L-norleucine phenylmethyl ester(222739-25-5)
• EPA Substance Registry System: 6-oxo-N-<carbonyl>-L-norleucine phenylmethyl ester(222739-25-5)

Safety Data

• Hazardous Substances Data: 222739-25-5(Hazardous Substances Data)

Upstream product

• 206867-88-1 phenylmethyl 2-amino-5-hexenoate 
• 108957-20-6 (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester 
• 193223-82-4 phenylmethyl 2-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hexenoate 
• 179815-16-8 dimethyl 2-H-hydroxy-2-<2-(propynyl)>pentanedioate 
• 179815-17-9 tetrahydro-5-oxo-2-<2-(propynyl)>-2-furancarboxylic acid 
• 141362-38-1 phenylmethyl (S)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hexenoate 
• 141362-49-4 phenylmethyl (S)-2-amino-5-hexenoate 
• 13192-04-6 dimethyl 2-ketoglutarate 
• 328-50-7 α-ketoglutaric acid 

Relevant articles and documents

Synthesis of the angiotensin-converting enzyme inhibitors (-)-A58365A and (-)-A58365B from a common intermediate

(-)-A58365A (1) and (-)-A58365B (2), which are inhibitors of angiotensin-converting enzyme, were synthesized from the subunits 9 and 10. These were coupled, and the resulting individual amides 17a,b were converted by ozonolysis into aldehydes 18a,b, which underwent cyclodehydration to the enamides 19a,b. Treatment with a stannane served to generate the vinyl stannanes 20a,b, from which ketones 22a,b were produced by protodestannylation and ozonolysis. Base treatment and hydrogenolysis then afforded (-)-A58365A (1). The intermediates 17a,b were also converted into aldehydes 26a,b by hydroboration and oxidation, and a similar sequence to that used for (-)-A58365A was then applied in order to complete the first enantiospecific synthesis of the congener, (-)-A58365B (2).